In this paper we examine the challenges of moving a large, traditionally waterfall-driven organization toward an agile development methodology. In particular we address the problems/successes we encountered in our attempts to adhere to the 12 practices of Extreme Programming given: 1) this was a first attempt with Agile techniques and in particular extreme programming and 2) an organization that while supportive, is still driven by its own set of governance processes which seem to be in contradiction to extreme programming. We discuss how we prepared our development and customer teams in order to achieve an agile mindset along with the issues we encountered in our attempts to mesh IBM?s internal processes with our implementation of Extreme Programming. Finally we address some of the lessons learned as revealed by our final project retrospective and out future plans using agile techniques